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Upcoming Events

Sun, Jun 07Enjoy an afternoon with one of West Michigan’s own! Toby Bresnahan joins us from 1:00 PM to 4:00 PM, bringing his signature mix of acoustic music and traditional Irish influences. From the festival stage to our tasting room, Toby’s music creates an inviting atmosphere you won’t want to miss.
RSVP ClosedSun, Jun 07Club members are invited to pick up their quarterly shipment and enjoy a complimentary food & wine tasting as a thank you for being part of the journey!
Wed, Jun 10Open Mic Night | Every Wednesday, 6:30–9 PM Step into a laid-back, welcoming space to play, practice, or simply enjoy the vibe. Bring your instrument—or just yourself—and be part of an evening filled with local talent and good energy.
Thu, Jun 11Reconnect with familiar faces and make new friends at our Thursday Night Game Night. From Euchre and Swoop to trivia and more, there’s something for everyone. Come with friends or fly solo—there’s always a seat at the table.


Wed, Jun 17Open Mic Night | Every Wednesday, 6:30–9 PM Step into a laid-back, welcoming space to play, practice, or simply enjoy the vibe. Bring your instrument—or just yourself—and be part of an evening filled with local talent and good energy.
Thu, Jun 18Reconnect with familiar faces and make new friends at our Thursday Night Game Night. From Euchre and Swoop to trivia and more, there’s something for everyone. Come with friends or fly solo—there’s always a seat at the table.
Sat, Jun 20We are thrilled to welcome the talented Jakob Abraham back to the winery! Join us on June 20th from 7:00 PM to 9:00 PM for an evening of exceptional live music and your favorite pours.
Wed, Jun 24Open Mic Night | Every Wednesday, 6:30–9 PM Step into a laid-back, welcoming space to play, practice, or simply enjoy the vibe. Bring your instrument—or just yourself—and be part of an evening filled with local talent and good energy.
Thu, Jun 25Reconnect with familiar faces and make new friends at our Thursday Night Game Night. From Euchre and Swoop to trivia and more, there’s something for everyone. Come with friends or fly solo—there’s always a seat at the table.
Fri, Jun 26Help feed our neighbors in need! Join us for a special evening with Sunrise Hicks as they return to support the local Northwest Osceola County Food Pantry in Tustin, Michigan. All band proceeds and tips from the night will be donated to help families in our community.
Sun, Jun 28Enhance your tasting experience with the talented Raylin Vance. She’s returning to the winery to provide the perfect keyboard music for an afternoon of great drinks and even better company.
Sat, Jul 11MOOD Music with Jeff Holoszko is back this summer, bringing all the feel-good vibes and great times. Enjoy his standout guitar playing, original songs, and favorite hits—the mood is always right when Jeff takes the stage.
Sat, Jul 18We are thrilled to welcome the talented Jakob Abraham back to the winery! Join us on June 20th from 7:00 PM to 9:00 PM for an evening of exceptional live music and your favorite pours.
Sat, Jul 25New band alert! We’re thrilled to host Broken Tip Jar for the very first time on July 25. Come out from 6:00 PM to 9:00 PM to hear their versatile blend of country, pop, and lite rock hits. From soulful acoustic vibes to a full-band sound, they’ve got something for everyone!
Sun, Jul 26Enhance your tasting experience with the talented Raylin Vance. She’s returning to the winery to provide the perfect keyboard music for an afternoon of great drinks and even better company.
Fri, Jul 31Experience the magic of live soul music at the winery with the talented J.R. Jenkins. From upbeat dance tracks to classic sing-alongs, it’s the perfect soundtrack for a memorable night at Cadillac Winery. Music from 6 - 9 PM.
Sat, Aug 08We are thrilled to welcome the talented Jakob Abraham back to the winery! Join us on June 20th from 7:00 PM to 9:00 PM for an evening of exceptional live music and your favorite pours.
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